Starting your own company is different from quitting in a huff or being fired. Usually those events come with too much angst to be enjoyable. You obsess. You look inward. It takes time to turn things around and feel good again.
Starting your own company is different because it very positively affects the way you feel about yourself in the world. This happens right away. You find yourself noticing trees and buildings you didn't see before. You feel the sun on your back and sense possibility when you get up in the morning. You're living by your wits, making your own way. It's an interestingly dangerous, open prairie kind of feeling. Like you're a gunslinger or a caveman or something.
Right after that, of course, you get scared shitless. But amazingly, that part doesn't really last. The peril has a way of becoming invisible. The fish stops noticing the water it swims in. I have way more financial stuff hanging in the balance now than ever before at work; I can't keep track of anyone or anything; there are probably ways in which we're leaking money like a torpedoed tanker. Yet I feel pretty good when I get up. Now, maybe that's just me. There are people I've spoken with who didn't like this feeling, who thought it was just too much pressure and stress. For me, though, and for a lot of people, I think working for yourself is creatively liberating in the best possible way. Samuel Johnson said that knowing you're going to die in two weeks focuses a man admirably. Same here—except for the death part, I hope. Having full responsibility has a way of making you pay closer attention, making you more alert and more open to the world of the new.
Another thing. When you don't work for yourself, you always feel like you're getting away with something when you have a good time at work. It seems to be a little bit at someone else's expense—the company, the client, the creative director who trusted you and would probably not particularly support that Chateau Lafitte Rothschild you just disguised in taxi receipts. Working for yourself, when you bury expenses, it's like burying a rock in your backyard. You're going to hit it with the lawnmower. You don't kid yourself. And you don't feel as guilty. There was an evening shoot, for instance, when we were counting on having a large traffic backup to film. When we got to the location, we saw only a handful of cars, zipping by above the speed limit. We got into my beat-up old Volkswagen, drove into the Caldecott Tunnel, made believe the car had broken down and created an instant traffic jam. Got the shot. Only problem was, the story leaked out to the local papers, making us look like reckless, selfish troublemakers (which, you know, I guess we were). Without a boss to answer to, however, this was much less of a problem. It was instantly just a funny production story.
There are risks and difficulties, of course. Beyond the obvious possibility of pyrotechnic financial disaster, I found that being a terrific creative director—which like any young writer, I had planned to pull off almost instantaneously, given even the slightest slack—was a lot thornier than anticipated. My first instinct was to act like I had always hoped my creative directors would act: I'd buy everything anybody suggested, so they'd think I was the best boss in the world. This resulted in a lot of happy people and a pile of really crappy work.
Once I was over that phase, however, I realized there were also so many attendant rewards—beyond money, I mean, which is nice, but also available when you work for someone else. I'm talking about having people love working inside the thing you all create together, having it change their lives, in some cases. And even if you rarely deserve it, you'll get credit for everything everyone does, which is cool. Especially if you're lucky enough, as I have been, to hang around with truly talented, unforgettable people.
So that's the insight, if there is one here. It's the promise of noticing the changes of season, a new fallen snow, clean windshield kind of feeling that you just won't quite get any other way. Do it at least once. You can always go back to what you're doing now.
If you don't have to, though, I can guarantee you won't.